5,5-dimethyl-3-(4-nitrophenyl)oxazolidine-2,4-dione | 1381863-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5-dimethyl-3-(4-nitrophenyl)oxazolidine-2,4-dione
• 英文别名: 5,5-dimethyl-N-(4-nitrophenyl)oxazolidine-2,4-dione；5,5-Dimethyl-3-(4-nitrophenyl)-1,3-oxazolidine-2,4-dione
• CAS: 1381863-03-1
• 化学式: C₁₁H₁₀N₂O₅
• 分子量: 250.211
• InChiKey: OMWIKPUCAZKHQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-羟基异丁酸甲酯 、 异氰酸对硝基苯 在 三乙胺 作用下， 以33%的产率得到5,5-dimethyl-3-(4-nitrophenyl)oxazolidine-2,4-dione
  参考文献：
  名称：

  N-Acyl and N-sulfonyloxazolidine-2,4-diones are pseudo-irreversible inhibitors of serine proteases

  摘要：

  The synthesis, inhibitory activity and mode of action of oxazolidine-2,4-diones against porcine pancreatic elastase, here used as a model for human neutrophil elastase, are reported. The nature of N-substitution at the oxazolidine-2,4-dione scaffold has large effect on the inhibitory potency against elastase. N-Acyl and N-sulfonyloxazolidine-2,4-diones emerged as potent pseudo-irreversible inhibitors, displaying high second-order rate constants for PPE inactivation. The title compounds were also shown to be potent inhibitors of human neutrophil elastase (HNE) and proteinase-3, and weak inhibitors of human cathepsin G. The results herein presented show that the oxazolidine-2,4-diones represent a new promising class of serine protease inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.093

文献信息

• <scp>Copper‐Catalyzed</scp> Modular Access to <scp> <i>N</i> ‐Fused </scp> Polycyclic Indoles and <scp>5‐Aroyl</scp> ‐pyrrol‐2‐ones <i>via</i> Intramolecular N—H/C—H Annulation with Alkynes: Scope and Mechanism Probes
  作者：Yan‐Hua Liu、Hong Song、Chi Zhang、Yue‐Jin Liu、Bing‐Feng Shi

  DOI：10.1002/cjoc.202000246

  日期：2020.12

  Copper‐catalyzed intramolecular N—H/C—H annulation with alkynes has been developed. A variety of densely functionalized heterocycles, such as pyrrolo[1,2‐a]indoles, indolo[1,2‐c]quinazolin‐2‐ones, oxazolo[3,4‐a]indoles, and imidazo[1,5‐a]indoles, were synthesized in an atom‐ and step‐economical manner, owing to the high modularized feature of aniline moiety, the linker moiety, as well as the alkyne

  已经开发了使用炔烃的铜催化分子内NH / CH环合反应。各种稠密官能化的杂环，如吡咯并[1,2- a ]吲哚，吲哚并[1,2 - c ]喹唑啉-2-酮，恶唑并[3,4- a ]吲哚和咪唑[1,5-由于苯胺部分，连接子部分和炔烃部分具有高度模块化的特征，因此以原子和分步经济的方式合成了α ]吲哚。通过简单地改变从二氧化剂叔将过氧化叔丁基（DTBP）转化为2,2,6,6-四甲基哌啶-1-氧基（TEMPO），该反应很容易转化为氨氧化途径，该途径从TEMPO夺取一个氧原子以生成5-芳酰基吡咯2个 机理实验表明，乙烯基自由基参与了该反应，而酰胺基自由基引发的自由基级联反应可能是造成这种转变的原因。